N-({(5S)-3-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide → N-({(5S)-3-[4-(1-methyl-6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

HRID 10828Notes

Reaction equation

HRID 10828 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:11][CH:10]=2)=[CH:3]1>CO.[Pd]>[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH:4]([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:13][CH:14]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 60083000N-({(5S)-3-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

Product 1

HCID 10315556N-({(5S)-3-[4-(1-methyl-6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamideYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of N-({(5S)-3-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.179 g. 0.52 mmol) in 20 mL of MeOH is added 0.05 g of 10% palladium on activated charcoal. The mixture is hydrogenated at 50 psi for 16 hours. The reaction mixture is filtered through celite, silica is added and the mixture is concentrated to dryness. The residue is loaded onto a SIM and purified on a Biotage 12S column with 2% MeOH in CH2Cl2 to yield the desired compound (0.175 g, 96%). 1H-NMR (DMSO) δ: 8.25, 7.41, 4.70, 4.10, 3.74, 3.39, 3.17, 2.83, 2.32, 2.01, 1.83

Workup

  1. filtrationThe reaction mixture is filtered through celite, silica
  2. additionis added
  3. concentrationthe mixture is concentrated to dryness
  4. custompurified on a Biotage 12S column with 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-5c6bb1e0d3264955b588e9c074389bb6
Source dataset
uspto-grants-2006_08
Patent number
US07094900B2

Reaction notes

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